3879-35-4

Upstream product

• 59-23-4 D-Galactose 
• 156-43-4 4-Ethoxyaniline 
• 100-63-0 phenylhydrazine 
• 50-99-7 D-glucose 
• 59-88-1 phenylhydrazine hydrochloride 
• 127-09-3 sodium acetate 
• 106-49-0 p-toluidine 
• 64-19-7 acetic acid 
• 62-53-3 aniline 
• 55905-50-5 O¹-methyl-D-fructose 
• 50-70-4 D-sorbitol 
• 7732-18-5 water 
• 7726-95-6 bromine 
• 66-84-2 D-(+)-glucosamine hydrochloride 

Downstream Products

• 15476-32-1 2-phenyl-4-(D-lyxo-1',2',3',4'-tetrahydroxybutyl)-2H-1,2,3-triazole 
• 75869-74-8 3,6-anhydro-D-lyxo-hexosulose 1,2-bis(phenylhydrazone) 
• 100738-94-1 2-phenylazo-1-(N'-phenyl-hydrazino)-D-xylo-1,5-anhydro-2-deoxy-hex-1-enitol 
• 113092-88-9 D-lyxo-[2]hexosulose-1-(ethyl-phenyl-hydrazone)-2-phenylhydrazone 
• 51073-57-5 cinnoline-3-carboxaldehyde 
• 4429-04-3 1-amino-1-deoxy-D-fructose 
• 3554-89-0 N-acetyl-4,5-di-O-acetyl-3,6-anhydro-L-lyxo-hexulose phenylosazone 
• 78077-10-8 4,5-di-O-acetyl-3,6-anhydro-L-lyxo-2-hexulose phenylosazone 
• 35522-78-2 3,6-anhydro-L-lyxo-2-hexulose phenylosazone 
• 104759-61-7 3,6-anhydro-β-L-threo-hexulose phenylosazone 
• 78147-91-8 4-(α-D-threofuranosyl)-2-phenyl-2H-1,2,3-triazole 
• 3554-89-0 N-acetyl-2,3-di-O-acetyl-3,6-anhydro-D-lyxo-hexulose phenylosazone 
• 78077-10-8 2,3-di-O-acetyl-3,6-anhydro-D-lyxo-hexulose phenylosazone 
• 79726-78-6 4-(2,3-O-isopropylidene-β-D-erythrofuranosyl)-2-phenyl-1,2,3-triazole 

Relevant academic research and scientific papers

Synthesis of Bioderived Cinnolines and Their Flow-Based Conversion into 1,4-Dihydrocinnoline Derivatives

Starting from phenylhydrazine and glucose, a versatile cinnoline scaffold was obtained on a multigram scale and further derivatized. A simple continuous-flow hydrogenation process permits the conversion of selected cinnolines into their 1,4-dihydrocinnoline counterparts. These products are generated in high yields and high purities with residence times of less than one minute and, along with their cinnoline precursors, are expected to serve as valuable heterocyclic building blocks for future medicinal chemistry programs.

Highly efficient and selective biocatalytic acylation studies on triazolylsugars

Different acid anhydrides (of C2 to C7 aliphatic fatty acids and benzoic acid) have been used to study the selective acylation of primary/secondary hydroxyl groups in 2-phenyl-4-(D-threo-1′,2′, 3′-trihydroxypropyl)-2H-1,2,3-triazole, 2-phenyl-4-(D-erythro-1′, 2′,3′-trihydroxypropyl)-2H-1,2,3-triazole, 2-phenyl-4-(D-arabino- 1′,2′,3′,4′-tetrahydroxybutyl)-2H-1,2,3-triazole and 2-phenyl-4-(D-lyxo-1′,2′,3′,4′-tetrahydroxybutyl)-2H-1, 2,3-triazole in the presence of Candida antarctica lipase B in diisopropyl ether. Among the different acid anhydrides, butanoic anhydride was found to be the most efficient acylating agent (for butanoylation); for acetylation, vinyl acetate gave the best results. The reactions with both these acylating agents were highly selective and efficient yielding exclusively the monoacylated products in 95-99% yields in 1-5 h.

REACTIONS OF ACETYLATED SUGAR OSAZONES WITH N OR O NUCLEOPHILES: SYNTHESIS OF 3-SUBSTITUTED AND 3,6-ANHYDRO DERIVATIVES

3,4,5-Tri-O-acetyl-D-erythro-pentosulose 1,2-bis(phenylhydrazone), its 1-N-acetyl derivative (D-erythro-4), 3,4,5,6-tetra-O-acetyl-L-xylo-hexosulose 1,2-bis(phenylhydrazone), and its 1-N-acetyl derivative have been treated with nucleophiles.Reaction of 3,

STUDIES ON 3-EPIMERIC 2-HEXULOSE PHENYLOSAZONES. STRUCTURE AND ANOMERIC CONFIGURATION OF THE 3,6-ANHYDRO-OSAZONE DERIVATIVES OBTAINED FROM D-arabino- AND D-ribo-2-HEXULOSE PHENYLOSAZONE

Dehydration of the 3-epimeric 2-hexulose phenylosazones D-arabino-hexulose phenylosazone or D-ribo-hexulose phenylosazone afforded 3,6-anhydro-D-ribo-hexulose phenylosazone (4) as the preponderant isomer from both.The identity of 4 was obtained by t.l.c., and by acylation followed by comparison of the products.Prolonged acetylation with acetic anhydride-pyridine, or by refluxing with acetic anhydride, afforded the same N-acetyldi-O-acetyl derivative.Refluxing 4 with copper sulfate, or the osotriazole with 20percent methanolic sulfuric acid, afforded the C-nucleoside analog, namely, 4-β-D-erythrofuranosyl-2-phenyl-1,2,3-osotriazole (7).The anomeric configurations of 4 and 7 were ascertained from the n.m.r. spectra of their isopropylidene derivatives.The mechanism of the dehydrative cyclization process and the mass spectra of two compounds were discussed.